Palladium‐Catalyzed Stagewise Strain‐Release‐Driven C−C Activation of Bicyclo[1.1.1]pentanyl Alcohols DOI
Songjie Yu,

Yinan Ai,

Lingfei Hu

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(24)

Опубликована: Март 25, 2022

A palladium-catalyzed chemoselective coupling of readily available bicyclo[1.1.1]pentanyl alcohols (BCP-OH) with various halides is reported, which offers expedient approaches to a wide range cyclobutanone and β,γ-enone skeletons via single or double C-C activation. The chemistry shows broad substrate scope in terms both the BCP-OH including series natural product derivatives. Moreover, dependency reaction chemodivergence on base additive has been investigated through experimental density functional theory (DFT) studies, expected significantly enrich modes increase synthetic potential preparing more complex molecules.

Язык: Английский

Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions DOI

Wenjun Han,

Jun‐Long Zhan,

Fang‐Long Yang

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(9)

Опубликована: Фев. 8, 2024

Abstract Cycloalkanols ring‐opening transformation is one of the most valuable and wide area research. Among numerous methods that have been developed, transition‐metal‐free approaches attracted great interest from both chemists pharmacologists. This largely due to advantages being environmentally benign, cost‐effective operationally simple. Here we provide a comprehensive outline on recent advances in synthesis distally substituted ketones cyclic compounds via cycloalkanols under conditions.

Язык: Английский

Процитировано

6

Improved Palladium Catalysis in Suzuki‐Type Coupling of Benzotriazinones for o‐Aryl/Alkenyl Benzamides DOI
Minling Xü, Ke Xü, Gang Zou

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(11), С. 2623 - 2628

Опубликована: Апрель 20, 2024

Abstract A palladium catalyst system based on PdCl 2 (PPh 3 ) or (dppf) is reported for Suzuki‐type coupling of both N ‐aryl and alkyl benzotriazinones with aryl/alkenyl boronic acids to afford a series ortho ‐aryl/alkenyl benzamides in yields up 99%, showing improvements catalytic efficiency, substrate scope practicality. Scope limitations the improved protocol have been demonstrated more than 40 examples, including multigram‐scale synthesis activated o ‐biphenyl amide. Large electronic steric effects from acid counterpart observed, implying transmetallation boron should be involved rate‐determining step cycle.

Язык: Английский

Процитировано

6

Visible-light-induced denitrogenative phosphorylation of benzotriazinones: a metal- and additive-free method for accessing ortho-phosphorylated benzamide derivatives DOI
Fushan Chen, Shanshan Hu, Sipei Li

и другие.

Green Chemistry, Год журнала: 2020, Номер 23(1), С. 296 - 301

Опубликована: Дек. 10, 2020

The first metal-free, visible-light-induced denitrogenative phosphorylation of 1,2,3-benzotriazinones is presented.

Язык: Английский

Процитировано

36

Construction of Bicyclic 1,2,3-Triazine N-Oxides from Aminocyanides DOI
Yuji Liu,

Xiujuan Qi,

Wenquan Zhang

и другие.

Organic Letters, Год журнала: 2020, Номер 23(3), С. 734 - 738

Опубликована: Дек. 15, 2020

Using a facile and cost-effective method, nine bicyclic 1,2,3-triazine 2-oxides were synthesized from o-aminocyanide substrates through an unusual nitration cyclization. The reaction mechanism was studied experimentally theoretically. Moreover, 3-oxides also obtained in good yields.

Язык: Английский

Процитировано

36

Ag-Catalyzed ring-opening of tertiary cycloalkanols for C–H functionalization of cyclic aldimines DOI
Jingjing Wang, Xue Liu,

Ziyan Wu

и другие.

Chemical Communications, Год журнала: 2021, Номер 57(12), С. 1506 - 1509

Опубликована: Янв. 1, 2021

Silver-catalyzed direct C–H functionalization of cyclic aldimines with cyclopropanols and cyclobutanols via a radical-mediated C–C bond cleavage strategy has been realized, generating the desired products in decent yields wide substrate scope.

Язык: Английский

Процитировано

32

Rh-Catalyzed cascade C–H activation/C–C cleavage/cyclization of carboxylic acids with cyclopropanols DOI
Siqi Wang,

Erfei Miao,

Hao Wang

и другие.

Chemical Communications, Год журнала: 2021, Номер 57(48), С. 5929 - 5932

Опубликована: Янв. 1, 2021

Merging both C–H and C–C activation in a tandem process is highly appealing but marked challenge.

Язык: Английский

Процитировано

31

Nickel-Catalyzed, Manganese-Assisted Denitrogenative Cross-Electrophile-Coupling of Benzotriazinones with Alkyl Halides for ortho-Alkylated Benzamides DOI

Fengze Wang,

Yi Tong,

Gang Zou

и другие.

Organic Letters, Год журнала: 2022, Номер 24(31), С. 5741 - 5745

Опубликована: Авг. 2, 2022

A nickel-catalyzed denitrogenative cross-electrophile-coupling of benzotriazinones with unactivated alkyl halides (X = Cl, Br, I) in the presence manganese powder as a reductant has been developed. The reaction furnishes ortho-alkylated secondary benzamides modest to good yields under mild conditions. scope is demonstrated 25 examples, showing tolerance steric hindrance and common functional groups, thus providing an efficient protocol benzamide derivatives without use preprepared organometallic reagents.

Язык: Английский

Процитировано

22

Trifluoroacetic Acid-Mediated Denitrogenative ortho-Hydroxylation of 1,2,3-Benzotriazin-4(3H)-ones: A Metal-Free Approach DOI

Kanagaraj Madasamy,

Madasamy Hari Balakrishnan,

Ramaraju Korivi

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(13), С. 8752 - 8756

Опубликована: Июнь 14, 2022

An efficient trifluoroacetic acid-mediated denitrogenative hydroxylation of 1,2,3-benzotriazin-4(3H)-ones is described. This metal-free approach compatible with a wide range 1,2,3-benzotriazin-4(3H)-ones, affording ortho-hydroxylated benzamides in good to high yields short reaction time. The believed proceed via benzene diazonium intermediate. synthetic utility the was successfully demonstrated by preparation an antimicrobial drug, Riparin C, and benzoxazine-2,4(3H)-diones yields.

Язык: Английский

Процитировано

20

Assembly of Benzo[c][1,2]dithiol-3-ones via Acid-Promoted Denitrogenative Transannulation of Benzotriazinones DOI
Yao Zhou, Bohao Zhang, Junjie Dong

и другие.

Organic Letters, Год журнала: 2022, Номер 24(49), С. 9012 - 9016

Опубликована: Дек. 5, 2022

An expedient synthesis of benzo[c][1,2]dithiol-3-ones via metal-free denitrogenative transannulation benzotriazinones is developed, which represents the first example acid-mediated heteroannulation benzotriazinones. This newly discovered reactivity enables streamline diverse in decent yields by using sodium sulfide as sulfur source under simple reaction conditions.

Язык: Английский

Процитировано

20

Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds DOI
Fatemeh Doraghi,

Seyedeh Pegah Aledavoud,

Azadeh Fakhrioliaei

и другие.

ChemistrySelect, Год журнала: 2023, Номер 8(32)

Опубликована: Авг. 23, 2023

Abstract Cyclopropanols, due to their particular chemistry, can participate in various synthetic reactions with retention or cleavage of the strained three‐membered ring. Direct cross‐coupling ring‐opening reaction such molecules access organic compounds, as ketones has great importance medicinal chemistry and material sciences. Hence, coupling reaction/cyclization cyclopropanols for constructing new valuable presence a transition metal catalyst under metal‐free conditions is described this context. The features are discussed, mechanisms challenging highlighted.

Язык: Английский

Процитировано

12